NPASS Compound

Natural Product: NPC266176

Natural Product ID	NPC266176
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(+)-Haemanthamine
IUPAC Name	n.a.
Synonyms	(+)-Haemanthamine; Hemeanthamin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL401114
PubChem CID	441593
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae alkaloids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 41 45 0 0 0 0 0 0 0 0999 V2000 -4.2306 2.0952 -1.6372 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9191 1.6989 -1.3655 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8691 0.6532 -0.4452 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1794 1.1223 0.7496 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0256 0.6746 1.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2758 -0.3560 0.4488 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7989 -0.6735 -0.9312 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2533 -0.5580 -1.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2416 -1.9895 -1.1433 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6503 -2.6936 0.0495 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3588 -1.7136 1.1480 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3819 -1.7038 2.0896 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1777 -2.0059 -1.2239 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8470 -0.8200 -0.6004 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1386 0.0023 0.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 1.0827 0.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0684 1.3863 0.5648 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9138 2.3977 1.0022 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0668 2.3399 0.1763 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0571 1.0175 -0.3727 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7496 0.5337 -0.2761 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1781 -0.5699 -0.8723 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1899 2.9244 -2.3717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7751 2.4125 -0.7353 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7779 1.2530 -2.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9374 0.4214 -0.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6624 1.8960 1.3432 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5785 1.0824 2.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2925 -0.0130 -1.6977 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5149 -0.4814 -2.1870 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8081 -1.4471 -0.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1093 -3.6548 0.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7296 -2.9730 0.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5982 -1.9620 1.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9408 -2.5036 1.9569 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6174 -2.8990 -0.6996 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4924 -2.1021 -2.2875 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2072 1.7737 1.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9676 3.0824 -0.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9812 2.5095 0.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7171 -1.2401 -1.5345 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 6 5 1 1 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 9 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 8 3 1 0 22 14 1 0 11 6 1 0 21 17 1 0 15 6 1 0 1 23 1 0 1 24 1 0 1 25 1 0 3 26 1 1 4 27 1 0 5 28 1 0 7 29 1 6 8 30 1 0 8 31 1 0 10 32 1 0 10 33 1 0 11 34 1 1 12 35 1 0 13 36 1 0 13 37 1 0 16 38 1 0 19 39 1 0 19 40 1 0 22 41 1 0 M END

Standard InCHIKey	YGPRSGKVLATIHT-HSHDSVGOSA-N
Standard InCHI	InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16+,17+/m1/s1
SMILES	CO[C@@H]1C=C[C@]23[C@H](C1)N(C[C@@H]2O)Cc1c3cc2OCOc2c1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	301.13	Volume:	295.418 ? Van der Waals volume.
Dense:	1.019	LogP:	1.085 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.207 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.444 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	23.0
TPSA:	51.16 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.79	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.217	Fsp³:	0.529
MCE-18:	94.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.229	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.201 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.014 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.295

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781	MDCK Permeability:	-4.686
Pgp-inhibitor:	0.051	Pgp-substrate:	0.59
PAMPA:	0.293 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.085	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.491

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.85	MRP1:	0.726
Plasma Protein Binding (PPB):	65.219%	Volume Distribution (VD):	0.404
Fu:	34.936% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.924
OATP1B3 inhibitor:	0.906	BCRP inhibitor:	0.027
BSEP inhibitor:	0.928

ADMET: Metabolism

CYP1A2-inhibitor:	0.692	CYP1A2-substrate:	0.459
CYP2C19-inhibitor:	0.641	CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.306	CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.974	CYP2D6-substrate:	0.976
CYP3A4-inhibitor:	0.026	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.006	CYP2C8-inhibitor:	0.0
HLM stability:	0.492 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.79

Half-life (T1/2):

2.62

ADMET: Toxicity

hERG Blockers:	0.19	hERG Blockers (10um):	0.464
Human Hepatotoxicity (H-HT):	0.683	Drug-induced Liver Injury (DILI):	0.48
AMES Toxicity:	0.702	Rat Oral Acute Toxicity:	0.809
Maximum Recommended Daily Dose:	0.888	Skin Sensitization:	0.616
Carcinogencity:	0.885	Eye Corrosion:	0.004
Eye Irritation:	0.678	Respiratory Toxicity:	0.912
Drug-induced Neurotoxicity:	0.579	Ototoxicity:	0.493
Hematotoxicity:	0.617	Drug-induced Nephrotoxicity:	0.715
Genotoxicity:	0.829	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.349	Hek293 Cytotoxicity:	0.441
BCF:	0.722 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.284 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.076 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.072 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1171883]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18356045]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO13120	Pancratium maritimum	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19500975]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	stem	n.a.	PMID[20066175]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25061748]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31513408]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13120	Pancratium maritimum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13120	Pancratium maritimum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13120	Pancratium maritimum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO672	Alangium salviifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13120	Pancratium maritimum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	34
Inhibition	2
GI50	54
Ratio IC50	5

Activity Type	# Activity
Individual protein	5
Cell line	84
Organism	5
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	IC50	=	452000.0	nM	PMID[19654408]
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	IC50	>	100000.0	nM	PMID[32309949]
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	6.0	%	PMID[32309949]
NPT439	Individual protein	Butyrylcholinesterase	Homo sapiens	IC50	>	100000.0	nM	PMID[32309949]
NPT439	Individual protein	Butyrylcholinesterase	Homo sapiens	Inhibition	=	13.0	%	PMID[32309949]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	23550.49	nM	PMID[17190440]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	16143.59	nM	PMID[16643028]
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	5128.61	nM	PMID[6481361]
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	16519.62	nM	DrugMatrix in vitro pharmacology data
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	14256.08	nM	DrugMatrix in vivo data: Pathology
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	13963.68	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	28575.91	nM	PMID[1965654]
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	14621.77	nM	PMID[20719504]
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[406395]
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	7673.61	nM	PMID[12713414]
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	46558.61	nM	PMID[20350950]
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	6471.43	nM	PMID[18550377]
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	14996.85	nM	PMID[21216145]
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	27925.44	nM	PMID[21868221]
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	41879.36	nM	PMID[16434194]
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	33342.64	nM	PMID[17595133]
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	14996.85	nM	PMID[25462220]
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	16557.7	nM	PMID[24754786]
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	30831.88	nM	PMID[23398362]
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	15488.17	nM	PMID[12086488]
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	12050.36	nM	PMID[18345611]
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	16672.47	nM	PMID[7473578]
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	5942.92	nM	PMID[19097894]
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	13520.73	nM	PMID[16643029]
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	18238.96	nM	PMID[20462236]
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	29580.12	nM	PMID[24697496]
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	3854.78	nM	PMID[12502321]
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	6382.63	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	9162.2	nM	PMID[23631483]
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	11694.99	nM	PMID[16621550]
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	23988.33	nM	PMID[22516426]
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	9057.33	nM	PMID[25237727]
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	15595.53	nM	PMID[18672931]
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	17418.07	nM	PMID[18494522]
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	29716.66	nM	PMID[24224794]
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	38018.94	nM	PMID[12088425]
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	79615.94	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	13614.45	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	19453.6	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	12882.5	nM	PMID[19786608]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	15739.83	nM	DOI[10.6019/CHEMBL1201861]
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	6223.0	nM	PMID[12699389]
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	19054.61	nM	PMID[23145884]
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	23120.65	nM	PMID[24025124]
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	20090.93	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	52480.75	nM	PMID[15921415]
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	8336.81	nM	PMID[10924160]
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	15275.66	nM	PMID[19754130]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	22646.44	nM	PMID[21856049]
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	25409.73	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	10423.17	nM	PMID[19371071]
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	18923.44	nM	DrugMatrix in vitro pharmacology data
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	18749.95	nM	PMID[26351041]
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	21827.3	nM	PMID[2045816]
NPT139	Cell line	HT-29	Homo sapiens	Ratio IC50	=	10.0	n.a.	PMID[19124664]
NPT65	Cell line	HepG2	Homo sapiens	Ratio IC50	=	10.0	n.a.	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	Ratio IC50	=	10.0	n.a.	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	Ratio IC50	=	10.0	n.a.	DOI[10.1016/j.cropro.2010.06.006]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	2100.0	nM	PMID[18494463]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	4800.0	nM	PMID[17341062]
NPT81	Cell line	A549	Homo sapiens	IC50	=	2500.0	nM	PMID[16643031]
NPT111	Cell line	K562	Homo sapiens	IC50	=	2500.0	nM	PMID[14980653]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	1400.0	nM	PMID[10780915]
NPT81	Cell line	A549	Homo sapiens	IC50	=	3000.0	nM	PMID[31513408]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	1300.0	nM	PMID[31513408]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	3700.0	nM	PMID[31513408]
NPT3190	Cell line	NHDF	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT81	Cell line	A549	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT196	Cell line	AGS	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT461	Cell line	PANC-1	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT2405	Cell line	SAOS-2	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT660	Cell line	SW480	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT457	Cell line	BT-549	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT2410	Cell line	NCI-H1299	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.7	ug.mL-1	PMID[3560159]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.75	ug.mL-1	PMID[31515186]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	0.49	ug.mL-1	PMID[31515186]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>=	1.95	ug.mL-1	PMID[31515186]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>=	1.8	ug.mL-1	PMID[31515186]
NPT21749	Cell line	COLO 201	Homo sapiens	IC50	=	300.0	nM	PMID[34536668]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	10.0	n.a.	PMID[23073993]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC266176 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18592
0.1-0.2	30382
0.2-0.3	794
0.3-0.4	54
0.4-0.5	19
0.5-0.6	7
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC158148
1.0	High Similarity	NPC290759
1.0	High Similarity	NPC82533
0.8413	Intermediate Similarity	NPC474470
0.7576	Intermediate Similarity	NPC244554
0.6875	Remote Similarity	NPC58766
0.6875	Remote Similarity	NPC475686
0.6716	Remote Similarity	NPC225597
0.6515	Remote Similarity	NPC78733
0.6056	Remote Similarity	NPC609368
0.5882	Remote Similarity	NPC247972
0.5616	Remote Similarity	NPC218614
0.5616	Remote Similarity	NPC607661
0.5417	Remote Similarity	NPC252960
0.5139	Remote Similarity	NPC65403
0.507	Remote Similarity	NPC215829
0.5067	Remote Similarity	NPC75958

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC266176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4499
0.1-0.2	4578
0.2-0.3	73
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data